TBPB-initiated cascade cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with sulfinic acids: access to sulfone-containing cyclopenta[gh]phenanthridines

Nengneng Zhou; Meixia Wu; Man Zhang; Xiaoqiang Zhou; Wei Zhou

doi:10.1039/D0OB00119H

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TBPB-initiated cascade cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with sulfinic acids: access to sulfone-containing cyclopenta[gh]phenanthridines†

Nengneng Zhou,

*^a Meixia Wu,^a Man Zhang,^a Xiaoqiang Zhou^b and Wei Zhou^a

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* Corresponding authors

^a Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China
E-mail: zhounn@ahnu.edu.cn

^b College of chemistry and material, Weinan Normal University, Weinan 714099, Shaanxi province, China

Abstract

A novel TBPB-initiated cascade cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with sulfinic acids via C–S, C–C and C–N bond formation for the synthesis of 3-sulfonated cyclopenta[gh]phenanthridines under metal-free conditions has been developed. This protocol features mild conditions, good functional group tolerance and a broad substrate scope. By using this protocol, a variety of potentially bioactive 3-sulfonated cyclopenta[gh]phenanthridines were facilely synthesized via direct annulation.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/D0OB00119H
Article type: Communication
Submitted: 18 Jan 2020
Accepted: 10 Feb 2020
First published: 10 Feb 2020

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Org. Biomol. Chem., 2020,18, 1733-1737

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TBPB-initiated cascade cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with sulfinic acids: access to sulfone-containing cyclopenta[gh]phenanthridines

N. Zhou, M. Wu, M. Zhang, X. Zhou and W. Zhou, Org. Biomol. Chem., 2020, 18, 1733 DOI: 10.1039/D0OB00119H

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Organic & Biomolecular Chemistry

TBPB-initiated cascade cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with sulfinic acids: access to sulfone-containing cyclopenta[gh]phenanthridines†

Abstract

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TBPB-initiated cascade cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with sulfinic acids: access to sulfone-containing cyclopenta[gh]phenanthridines

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